Fool the Family
by MercyFrost
Summary: A concerned grandmother, a disapproving father and overprotective brother put Tess and Oliver into a corner. And the only way out...a fake partner. How can Chloe not intervene?
1. Chapter 1

A/N: Hello, everybody! School has had me on a sort of hiatus that feels like forever. Now, last year I wrote a holiday story called Holiday Matchup, which got one of the best responses I've ever gotten on a story. I've also gotten a lot of encouragement to continue it. Unfortunately, I, for the life of me was unable to figure out a way to continue the story line. So, I did what I did last year and based the story off of a Hallmark movie. I believe this one is based of of 'Hitched for the Holidays.' I'm posting this as I write it for the most part so updates may be sporadic as I am super busy but will do my absolute best to update in a timely manner. Thea is from the show Arrow. And Tess was never given up for adoption and Lillian is alive. You can figure it out from there.

Tess pulled the door open and stepped inside the giant Luthor mansion. A poor little maid running into the room, apologizing profusely and taking her coat, but Tess just smiled, nodded and headed toward the living room where Lex, Lana, Lionel, and Lillian were reclined.

Tess fluffed her hair and took a deep breath before entering the room with the most diplomatic smile she could muster. She took a seat on the love-seat whose second seat remained empty, she dourly noted. And she wasn't the only one who noticed. Lana and Lillian looked positively distress and Lionel disappointed. Only Lex was ignorant, probably through sheer force of will.

Lex and she had always been close and as a consequence Lex had always been very protective of his little sister. Lex had been the one to grill her high school boyfriends and when she gets married he'll be the one who'll have to be asked for her hand.

Lionel, on the other hand, thought it was an absolute disgrace that his daughter was so consistently single. But Tess and her father's relationship had always been strained since Lex was the obvious favorite. Tess had retaliated by pulling out of Luthorcorp and building up another company from their downward spiral and turned it into Mercy Industries, which could now play with the big guns like Queen Industries and Wayne Tech, making Lionel even more upset that she was successful. Though he blamed it on her close relationship with the Frost brat, Emma even though they lost touch ages ago.

Lillian frowned deeply. She was Lionel's polar opposite and loved Tess even though she wasn't even her child. She did her best to treat her the same as Lex though it was not exactly as successful as she would have hoped.

Lana looked downright disappointed. Lex had started dating her a few years ago and they had been married for a year and a half. Lana looked at Tess like the big sister she never had and every time she came home alone Lana insisted on setting her up, and Tess had been refusing every time. But it was moments like these that almost made her want to give in.

Lionel cleared his throat. "Welcome back, Tess, it's good to see you."

Tess smiled as she always does and says, "thank you, Father, you too."

Lionel leaned, his eyes baring into hers as venom passed between them viciously, but keeping it quiet so as not to start anything. "I saw you made a move on the headquarters in Germany."

A smirk tugged at the corner of lips and a spark of superiority leaped into her eyes and danced in a thinly veiled blaze. "I take it you saw the press release."

"I must give you credit, Tess, you are unpredictable. I didn't think you would move on it for another few months." Tess was wary. She knew he had something up his sleeve, she just needed to find out what. "I would have waited."

She smirked, and leaned forward as though confiding in him. "I know you would've." Lex fought a smile and a chuckle at his sister's daring, earning an elbow to the ribs from Lana.

Lillian attempted diplomacy. "Let's not talk business. Let's just be a family instead of business rivals," she implored Lionel who huffed but agreed.

All Tess could think was, as if.

Oliver pushed through the door with a bright smile. He shrugged off his coat and walked into his grandmother's living room. His sister, Thea, and her boyfriend, Roy, was seated across from their grandmother. He held up a hand in greeting with a broad smile still painted across his face. Grandma smiled brightly at the sight of her grandson but when Thea looked back she looked slightly outraged and more than a little panicked.

"Oliver where's your girlfriend?" Thea asked forcefully, clearly a loaded question to which a wrong answer would be fatal.

"Ah," Oliver stuttered, "you didn't get my text?" Even Roy could tell Oliver was clueless and he was usually so scared of him that he didn't even bother to try to read him.

Their grandmother looked so wholly disappointed that anyone with a heart would have felt it break. "Thea promised she would be coming tonight."

"Family emergency," Oliver lied, "she didn't get the chance to talk cuz she had to go so I don't know what happened. But she's excited to meet you," Oliver added.

Her face broke out into the biggest smile he could remember ever seeing on her face. "Well, I'll go get you some cocoa." With that she waddled out to the kitchen.

With that brother and sister whirled on each other while Roy face-palmed, knowing what was coming. "Don't you two communicate?"

"You told me you were bringing somebody!" Thea hissed.

Oliver feigned innocence. "Really? I don't remember saying that." Roy winced, knowing that would only make her more angry.

"Oliver!"

"Thea!"

Tess groaned with her head in her hands. She was out with her best friend, Chloe. "It was torture, Chloe. He sat there the whole time with that smug smirk on his face because I didn't have a date yet again." Chloe smiled sympathetically at her friend.

"Maybe you should just bring a date?" she offered warily with a half-hearted shrug, careful of her reaction.

Tess glared at her annoyed, "if I could I would. But I work too much."

Chloe shook her head in defeat. "I don't know, Tess, there's got to be somebody."

Tess sighed, pinching the bridge of her nose. "Not that I know of, Chloe, not that I know of."

Oliver sighed dropping into a chair and sinking down into it, running his hand down his face. "Merry Christmas, Oliver." He just received a groan in response.

"This is my friend, Jimmy," Clark motioned at the man sitting on the chair beside him. Oliver didn't look up. "Oliver," Clark snapped making Oliver jump awake.

He shook his head in an attempt to wake himself up, rubbing the bridge of his nose. "Sorry, man." He turned his attention to Jimmy. "Hey...uh," he stopped realizing that he had no clue a to what his name was.

"Jimmy," Clark supplied.

"Jimmy," Oliver finished quickly, as though he didn't need help.

"Rough night?" Jimmy asked with an innocently mocking laugh.

Oliver groaned, shaking his head, "you have no idea." He looked up at the two men desperately, "I have to find a girlfriend by tomorrow night so my sister won't set me up so my grandmother will chill."

Clark frowned. "How're you planning to pull that off?"

Oliver shrugged with a blank expression. "I don't know."

When Jimmy got back to the house Chloe was already on the couch leafing through a magazine in search of a great sale on the perfect gift. More often than not they just ended up buying gift cards. "Hey," he announced himself.

Chloe looked up with a smile. "Hey, you. How'd it go?"

Jimmy shrugged dropping into the chair beside the couch she was resting on. "Fine, I guess. Oliver seemed to have a rough night."

Chloe rolled her eyes, "Only Oliver would go drinking the night before he's supposed to meet someone."

Jimmy looked slightly panicked at getting Oliver in trouble. "No, actually it has more do with him having to get a fake girlfriend to fool his grandmother by tomorrow night."

A devilish smile appeared on Chloe's face, her eyes twinkling. "Chloe..."


	2. Chapter 2

Tess stared at her friend in the least judgmental way she could manage. "You know how I feel about set ups," she answered sternly, with a matching emerald glare.

Chloe pleaded with only a smile, practically begging with just her eyes. Honestly she had been waiting for Tess to get a boyfriend for a while now. She had just never thought to put Tess and Oliver...together. Now that she thought of it, it made so much sense.

Tess needed someone who could laugh at her anger spurts and see through those walls she put up. Who better than the man who could laugh at anything and had those same walls? Oliver needed someone who could call him out on his crap but comfort him when he needed it, someone who could read him. Tess could read anyone to the point it was kinda scary. She was also the only person capable of stopping Chloe if her lead was too dangerous, surprising her by being able to comfort her when she and Jimmy had that huge fight. She's so blind to have not seen it before. "Tess, come on, what could it hurt? It' sustain for the holidays."

Tess' glare didn't stagger. Chloe bit her lip. "You actually don't have as much of a choice as I let on." Tess' eyes held their intensity but narrowed in suspicion. "He's waiting outside," Chloe tilt her head with a triumphant smile, knowing she won't send him away without meeting him first.

Chloe stood up and waved to get his attention and motioned for him to come in. He strut in as Tess watched with wary _eyes._ Ollie was startled by the intensity of the green in her eyes and the cool veneer with which she watched him approach. He sat down and attempted the charming smile that he usually charmed people with. Nothing changes in the redhead's demeanor except her eyebrow popped up her head.

As her eyebrow lowered a smirk spread across her face. She leaned forward, studying him as Chloe grit her teeth, wary of Tess' reaction to Oliver's introduction. She knew whatever was going to happen was going to happen and she could no longer intervene, which was a problem since it didn't appear to be going well.

Tess' studying eyes rested on his brown ones intently and Oliver shockingly didn't mind. They were beautifully captivating in a way that surprised him with the fact that he didn't mind. His smile slowly faded as he just watched her watch him. Her gaze remained guarded but his turned studious.

"Ahem," Chloe cleared her throat. To her it just looked like they were having a staring contest to the death.

Tess' head turned to meet Chloe's eyes accusingly as Oliver leaned back in his chair in an attempt to make himself comfortable again. "I didn't realize Oliver Queen was the "friend" you were referring to."

Oliver's face screwed up in confusion. "I'm sorry who're you, little miss merciful."

Chloe shook her head furiously, attempting to warn him so desperately not to try anything stupid but to no avail. Tess' gaze cut cleanly toward the playboy. "Lutessa Luthor," she answered scornfully.

Oliver leaned forward in outrage, fully prepared for an argument with cannons at the ready when he was interrupted. "Tess?"

Tess, Oliver, and Chloe's eyes darted to the bald man waving at them from the entrance. Chloe's eyes drifted to Tess in the hope of what the redhead does best. Thinking on the spot. Fortunately for Chloe, she only saw one option and Chloe was very smug by its existence. Oliver fumbled for words as Tess' face lit up in a smile that Chloe knew had nothing to do with his presence. "Lex," she greeted, giving her big brother a hug. Oliver forced a smile, though not as easily or as graceful as Tess' lie.

Suspicion flickered over Lex's face as Oliver rose and shook his hand. Things had gotten better between Ollie and Lex but not to the point where Oliver should have been as delighted to see him as he was trying to make it out to be. "Oliver, what're you doing here?" he asked, forcing the growing suspicion out of his voice and masking it was jovial curiosity.

As Oliver fumbled for words he desperately looked at Tess and then at Chloe, who had been sitting back and observing the conversation. Tess restrained from rolling her eyes and forced herself to blush lightly, not so much that it was suspicious but just enough for Lex to notice. "You weren't supposed to find out until tonight but I guess I should tell you now."

Always one for theatrics she took a deep breath and moved to Oliver's side, taking his hand in both of hers, faux fond gesture. "Oliver and I are dating."

Now Oliver didn't have to force his smile as she rested her head on his shoulder. He just had to make sure it looked more loving than the triumph he was actually feeling. He was interested to get to know the stunning redhead beside him, and her hatred of him, probably for his actions toward her older brother in high school, only further intrigued him.

Lex blinked and Chloe watched warily as he looked from her to Oliver to Tess as he wondered when the world had begun to spin off of its axis. "We'll talk more about this later. I have a meeting to get to." He turned around and walked out without another word.

Chloe pursed her lips, watching the bald man leave. "He forgot to get coffee."

Tess untangled herself from Oliver and spat in Chloe's direction. "I think he has bigger concerns at the moment."

A smirk tugged at Oliver's lips at her fury. It really was rather endearing. "Why? Because his sister's dating an infamous playboy?"

She sighed. "To start," she admitted.

Oliver stood up. "We going to mine or your's first?" He still looked far too smug for his own good.

"Your's," she answered curtly, refusing to meet either blondes' eye.

Oliver stood up, clapping his hand together with a gleeful glint in his eye. "Well, I have a meeting to get to. See you tonight, Mercy." He traipsed out the door, smirk still twitching at the corner of his lips.

Tess turned her head to face Chloe, who was looking at her in smug amusement, her eyes twinkling. "Don't look so triumphant," Tess bit out scornfully.

A/N: I'll be honest I updated a lot faster than I expected to. Yay! Okay, I know it's still not _quick _but still. Please review?.


	3. Chapter 3

Tess folded into the car, as he slammed the door behind her, walking around the car and sliding into the driver's seat beside her. "There's not really much you need to know going into this. You're Lex's sister so you must be pretty smart. My sister and her boyfriend will be there so anything you get stuck on, one of us will help you out." He gave his whole spiel facing forward, eyes on the road, one hand on her wheel with his body turned slightly toward her while his head remained face forward. He appeared relaxed even though he was really quite tense.

Tess nodded, noting the stiffness in his shoulders, her eyes traveling up and down his body studiously. With the realization that she was staring she snapped forward to attention. "I'm sure I'll figure it out."

The car swung into a small, quaint house with no distinct features but vaguely resembled something from an old disney movie about the North Pole, especially decorated as it was. Oliver sighed, pulling the key out of the ignition. "She's very festive," he explained at Tess' cool scrutinization.

She looked at him, a faint smile softening her face. "I can tell," she replied. Though this time it was not as spiteful as he would have thought she would say it. Instead it seemed mildly teasing and even slightly fond.

"You ready to pretend not to hate me?" He asked, avoiding deciphering the expression anymore than he has to.

Her soft smile morphed into a devilish smirk as she smoothly whispered, "I don't think it'll be as difficult as you seem to think." She stepped out of the car, leaving him wondering whether or not she was flirting with him.

Shaking his head, he got out of the car and followed her to the front door and knocked. They waited silently, awkward tension hanging between them. The door swung open and Thea stood on the other side. "This is the girl you suckered in to coming with you?" She was joking, but the subtext was there.

Tess shrugged. "Consider it mutual benefit." Her cool demeanor shocked Thea. She was expecting some bimbo with a boob job. She was certainly not that. Instead of responding she swung the door open and stepped aside letting them enter.

Tess was also mildly surprised. She was expecting some brat whose eyes rolled enough to roll right out of her sockets. But Thea didn't seem to be that so she'll take it.

"Roy's in there." She motioned toward the living room. "He's in on this," she explained exclusively to the redhead, who simply nodded, trying to make the best of an awkward situation.

"Thea, dear, is that Ollie?" an obviously old woman's voice called from the living room.

"Yeah," she called back, a grin starting to creep up on her face, excitement starting to get the best of her, "and he brought his date."

Ollie did his best to hide his gulp as Tess steeled herself, pushing her shoulders back and determination lighting in her eyes. If this went well then Oliver would be encouraged to do well, which would probably be more difficult seeing as she just had to fool some half-blind old lady. Oliver on the other hand had to fool Lionel Luthor. Entirely different ballpark.

She took his hand in hers and let him lead her forward, falling into the role with ease as she began to put on the show that she had been preparing for. Thea followed in after, suspicion blooming at the ease with which Oliver reacted. Easy, affectionate gestures were never his thing. Over zealous flirting and anything beyond that he had down but those small gestures, holding hands, gentle smiles, which Tess seemed to have down so well were completely foreign to him and Thea knew it. So the way he fell into it so easily astonished her and she knew Grandma would notice as well, no matter how soft she seemed to be growing her senses were still as sharp as they had been 50 years ago, especially when it came to her grandson.

Roy rose and shook hands with Oliver, giving him a slap on should and a "good to see you," from either side. Tess smiled and shook his hand, amicably appropriate. Tess walked to the chair that Grandma was sitting in and shook her hand with a kind smile, introducing herself. The old woman positively glowed with joy. "Pleasure to meet you, dear. When Oliver mentioned he was seeing someone I just couldn't wait to meet her. Tell me how long have you been dating?" She directed toward the pair, eyes flicking between both of them.

Tess looked back feigning delight and looks back at Ollie before turning back to Grandma as she'd been instructed to call her, and told her, "I'd be surprised if he knew to be honest."

Grandma swatted at her facetiously, so over the moon by her mere presence that Tess didn't even have to try. "Oh, I'm sure he does," she admonished gayly.

Oliver grimaced. How long was appropriate? He looked to Tess in desperation for help and she laughed, genuinely too, at his worry. The truth was, she wasn't oblivious to how adorable he looked when he was like that, especially when he let the act drop. It was these moments that she caught herself developing the slightest crush on him, though she would never admit that, not even to herself because that would mean her heart had turned back on and she couldn't let that happen, not again. "A little over a month," She explained in faux patience.

He nodded and repeated, "a little over a month."

Walking out he looked over at her, with her arms crossed in a poor attempt to keep herself warm, this evident failure placing a small pout on her lips that made him smile at her. "That went well."

Tess looked up to him in honest curiosity. "/Did it?"

Oliver smiled that cheeky smile he had and said, "it went so well that Thea might be plotting ways to get you to stick around." Tess smiled at that too. He said it as a mocking threat, but after tonight, and how he was with his family, she couldn't help but think that might not be such a terrible idea.

a/n: first off, I apologize for the lack of updates. There are two ways I could go with this. Considering this is a holiday story I don't want it to go on for too much longer so I can either end this with the next chapter to keep it going and hope that this doesn't go until June. Feedback would be appreciated and as soon as possible so I know what I'm doing.


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